EP0501735A1 - Antistatische Oberflächenmodifikation von Polymerisaten - Google Patents
Antistatische Oberflächenmodifikation von Polymerisaten Download PDFInfo
- Publication number
- EP0501735A1 EP0501735A1 EP92301546A EP92301546A EP0501735A1 EP 0501735 A1 EP0501735 A1 EP 0501735A1 EP 92301546 A EP92301546 A EP 92301546A EP 92301546 A EP92301546 A EP 92301546A EP 0501735 A1 EP0501735 A1 EP 0501735A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- antistatic agent
- solvent
- ammonium bromide
- antistatic
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/06—Coating with compositions not containing macromolecular substances
- C08J7/065—Low-molecular-weight organic substances, e.g. absorption of additives in the surface of the article
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/044—Forming conductive coatings; Forming coatings having anti-static properties
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2327/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/04—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08J2327/06—Homopolymers or copolymers of vinyl chloride
Definitions
- This invention is directed to imparting antistatic properties to a thermoplastic polymer, preferably a polyvinyl chloride polymer.
- Antistatic agents have been applied to polymers by either an external or an internal method.
- the external method which generally involves dipping or wiping a solution of antistatic agent on the polymer, has heretofore been inadequate.
- the external process due to the nature of the solvent used, generally alcohol or water, does not result in an adequate incorporation of the antistatic agent into the polymer, and thus, results in almost complete loss of the antistatic property following washing.
- the internal method which generally involves incorporation of an antistatic agent into the polymeric material prior to shaping into solid form, has also heretofore been inadequate.
- the internal process has been largely uneconomical and inefficient because the antistatic agent is present substantially in the interior of the shaped article, where it does not function effectively to prevent surface static properties.
- the internat process is also limited in the choice of antistatic agents and requires significantly large quantities of antistatic agent.
- the problem addressed by the present invention is to provide new methods of conferring antistatic properties to thermoplastic polymers, materials for treating the polymers, and thermoplastic polymers obtainable thereby.
- the invention relates to PVC polymers.
- the present invention provides a permanence because the antistatic agent in the present invention exists not only on the surface of the PVC but also penetrates through the surface of the PVC.
- the PVC may be contacted with the solution containing the antistatic agent in various ways.
- the contacting may involve a dipping, spraying, wiping, coating, or other the process, provided that the PVC and the antistatic agent solution are contacted for a sufficient time to allow the antistatic agent to penetrate into the PVC.
- the process disclosed in US-A-4770905 may be used.
- the PVC and the antistatic agent solution are contacted for a sufficient time to allow the antistatic agent to penetrate into the PVC, the PVC can be washed with water and then subsequently dried.
- R1 and R2 are selected such that they are soluble in the solvent and insoluble or only slightly soluble in water.
- R1 and R2 can each be a substituted or non-substituted alkyl group of from 1-20 carbon atoms.
- Examples of the (hexyl) n (octyl) m ammonium bromide antistatic agent are bihexyl bioctyl ammonium bromide, trihexyl octyl ammonium bromide, and tetrahexyl ammonium bromide.
- Examples of the (heptyl) n (octyl) m ammonium bromide antistatic agent are biheptyl bioctyl ammonium bromide, triheptyl octyl ammonium bromide, and tetraheptyl ammonium bromide.
- the ammonium halide antistatic agents are typically preferred over the 1-dodecylpyridinium antistatic agent because the ammonium halide antistatic agents are water insoluble but solvent soluble.
- the 1-dodecylpyridinium antistatic agent is somewhat soluble in water and, hence, some of it may be removed from the PVC during washing. Nevertheless, the 1-dodecylpyridinium antistatic agent can be effectively used.
- the solvent used for contacting the antistatic agent with the PVC can be any solvent which swells the PVC surface and which is soluble with the antistatic agent.
- the solvent can be methylene chloride, dimethyl sulfoxide (DMSO) or N-methyl pyrrolidone (NMP).
- the antistatic agent concentration by weight in the solvent is preferably from about 1% to about 30%, and more preferably from about 10% to about 20%.
- the solution containing the antistatic agent is contacted with the PVC preferably from about 2 to about 60 seconds.
- PVC samples (89 x 89mm) were dipped in a methylene chloride solution containing various concentrations of 1-dodecylpyridinium chloride monohydrate. Following the dipping process, the sample was washed with water and air dried.
- the effect of the treatment was then evaluated by measuring the Surface Resistivity (Rs) and the Decay Time (sec).
- the Surface Resistivity was measured according to ASTM D257 and the Decay Time according to the Fed. Test Method STD No. 1010, Method 4046. Untreated samples were also measured for comparative purposes.
- the antistatic agent/CH2Cl2 embodying the invention also exhibited at least a 30 day degree of permanence as shown by the Rs values on day 1 and day 37 (see Table I).
- PVC samples were dipped in a methylene chloride solution containing various concentrations of tetrahexyl ammonium bromide in the same manner as in Example 1.
- Table 2 shows the results for the as treated samples.
- Table 3 shows the degree of permanence after various post-treatments.
- Table 4 shows the degree of permanence as a function of time.
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Treatments Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/662,206 US5169688A (en) | 1991-02-27 | 1991-02-27 | Antistatic surface modification of pvc |
US662206 | 1991-02-27 |
Publications (1)
Publication Number | Publication Date |
---|---|
EP0501735A1 true EP0501735A1 (de) | 1992-09-02 |
Family
ID=24656805
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP92301546A Withdrawn EP0501735A1 (de) | 1991-02-27 | 1992-02-25 | Antistatische Oberflächenmodifikation von Polymerisaten |
Country Status (4)
Country | Link |
---|---|
US (1) | US5169688A (de) |
EP (1) | EP0501735A1 (de) |
JP (1) | JPH05214130A (de) |
CA (1) | CA2061605A1 (de) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994011421A1 (en) * | 1992-11-06 | 1994-05-26 | Pharmacia Biotech Ab | A method of surface modification |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN112521698A (zh) * | 2020-12-09 | 2021-03-19 | 宁波保税区君一汽配科技有限公司 | 一种pvc塑料及其制备方法 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR1293186A (fr) * | 1960-04-14 | 1962-05-11 | Ici Ltd | Polymères organiques à propriétés antistatiques améliorées |
GB921032A (en) * | 1958-11-27 | 1963-03-13 | Tokyo Shibaura Electric Co | A method of manufacturing antistatic record discs |
EP0134523A1 (de) * | 1983-08-04 | 1985-03-20 | General Electric Company | Absorption von Additiven aus Lösungen in Polymeroberflächen |
US4770905A (en) * | 1986-12-23 | 1988-09-13 | M&T Chemicals Inc. | Process for surface modification of polymer articles |
Family Cites Families (42)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2125827A (en) * | 1936-12-24 | 1938-08-02 | Bakelite Corp | Coating articles |
CA721243A (en) * | 1957-08-01 | 1965-11-09 | E. Amborski Leonard | Organic polymeric structures |
NL260065A (de) * | 1962-01-13 | |||
US3192074A (en) * | 1962-09-04 | 1965-06-29 | Amchem Prod | Method of applying a chemical conversion coating solution to a metal surface |
US3297462A (en) * | 1963-09-10 | 1967-01-10 | Du Pont | Process for rendering organic polymeric shaped structure resistant to degradation by ultraviolet light |
US3309220A (en) * | 1964-04-10 | 1967-03-14 | Gen Electric | Method of producing an ultraviolet resistant polycarbonate article |
US3519462A (en) * | 1966-03-21 | 1970-07-07 | American Cyanamid Co | Method of impregnating polymethyl methacrylate |
US3617330A (en) * | 1967-03-09 | 1971-11-02 | Bayer Ag | Mouldings of polycarbonates with improved surfaces and process for their production |
US3594264A (en) * | 1968-10-28 | 1971-07-20 | Gen Electric | Ultraviolet light stabilized polycarbonate article |
FR2120511A5 (fr) * | 1971-01-06 | 1972-08-18 | Solvay | Procede pour proteger des objets en matiere plastique contre la photodegradation due au rayonnement solaire et produits ainsi obtenus |
DE2211641C3 (de) * | 1972-03-10 | 1975-08-21 | Bayer Ag, 5090 Leverkusen | Verfahren zur Stabilisierung von Formteilen aus hochmolekularen thermoplastischen Polycarbonaten |
IL39037A (en) * | 1972-03-20 | 1975-02-10 | Jochanan R | Uv-and oxidation-proof products from organic plastics and their manufacture |
CA1027428A (en) * | 1972-06-22 | 1978-03-07 | Walter H. Engel | Plastic article of manufacture impregnated with volatile matter and method and apparatus for making the same |
US4210556A (en) * | 1974-01-24 | 1980-07-01 | Akzona Incorporated | Solid antistatic compositions |
FR2360401A1 (fr) * | 1976-08-04 | 1978-03-03 | Solvay | Procede pour la production de feuilles orientees en resine thermoplastique protegees contre l'action des rayons ultraviolets |
US4129667A (en) * | 1977-12-29 | 1978-12-12 | Gaf Corporation | Radiation curable coating composition comprising an acryl urethane oligomer and an ultra-violet absorber |
DE2808036A1 (de) * | 1978-02-24 | 1979-08-30 | Solvay Werke Gmbh | Mittel und verfahren zur verbesserung der wetterbestaendigkeit bzw. lichtbestaendigkeit von formteilen bzw. gegenstaenden aus polyvinylchlorid |
DE2808005A1 (de) * | 1978-02-24 | 1979-08-30 | Solvay Werke Gmbh | Mittel und verfahren zum regenerieren und vergueten verlichteter bzw. verwitterter oberflaechen bzw. oberflaechenschichten von formteilen bzw. gegenstaenden aus thermoplastischen kunststoffen |
US4146658A (en) * | 1978-04-12 | 1979-03-27 | General Electric Company | Process for producing an ultraviolet light stabilized polycarbonate article |
US4276138A (en) * | 1978-06-27 | 1981-06-30 | Agency Of Industrial Science & Technology | Method for reducing electrostatic charging on shaped articles of polyvinyl chloride resins |
US4349607A (en) * | 1979-09-05 | 1982-09-14 | General Electric Company | UV Stabilizers, coating compositions and composite structures obtained therefrom |
US4353959A (en) * | 1979-12-21 | 1982-10-12 | General Electric Company | Abrasion resistant silicone coated polycarbonate article having an acrylic primer layer containing a U.V. absorbing compound |
US4349602A (en) * | 1980-05-30 | 1982-09-14 | General Electric Company | Substrates coated with a thermoset acrylic primer and an alkoxysilylbenzotriazole UV stabilizer |
US4322455A (en) * | 1980-09-15 | 1982-03-30 | General Electric Company | Process for producing an ultraviolet radiation stabilized polymeric article |
US4323597A (en) * | 1980-09-15 | 1982-04-06 | General Electric Company | Process for producing an ultraviolet radiation stabilized polymeric article |
US4396678A (en) * | 1981-04-10 | 1983-08-02 | General Electric Company | Coated surface stabilized polycarbonate article |
US4382109A (en) * | 1981-08-07 | 1983-05-03 | General Electric Company | Abrasion resistant silicone coated thermoplastic article and method for making |
US4439494A (en) * | 1982-03-01 | 1984-03-27 | General Electric Company | Silyl-polyacrylates for polycarbonate substrates |
US4511489A (en) * | 1983-06-01 | 1985-04-16 | The Drackett Company | Composition for cleaning and imparting antistatic properties to plastics surfaces |
US4792492A (en) * | 1983-08-04 | 1988-12-20 | General Electric Company | Absorption of additivies into polymer surfaces from solution |
US4547414A (en) * | 1983-09-01 | 1985-10-15 | Kitagawa Industries Co., Ltd. | Room temperature shrinkable coating material |
US4556606A (en) * | 1983-12-30 | 1985-12-03 | General Electric Company | UV-Stabilized coated polyester-carbonate articles and process |
AU573647B2 (en) * | 1984-01-30 | 1988-06-16 | General Electric Company | Uv-stabilised polymer compositions |
US4636408A (en) * | 1984-01-30 | 1987-01-13 | General Electric Company | Ultraviolet radiation stabilized polymer compositions |
JPH0613620B2 (ja) * | 1984-12-17 | 1994-02-23 | 株式会社アサヒコーポレーション | 帯電防止性靴底用ゴム組成物 |
US4792465A (en) * | 1986-12-23 | 1988-12-20 | M&T Chemicals Inc. | Process for making surface modified U.V. stabilized PVC articles |
US4913082A (en) * | 1986-12-23 | 1990-04-03 | M&T Chemicals Inc. | Process for surface modification of polymer articles |
US4868011A (en) * | 1986-12-23 | 1989-09-19 | M&T Chemicals Inc. | Process for surface modification of polymer articles |
US4925739A (en) * | 1987-07-23 | 1990-05-15 | M&T Chemicals Inc. | Surface modified polymer article and process for making same |
US4865880A (en) * | 1986-12-23 | 1989-09-12 | M&T Chemicals Inc. | Surface modified, U.V. stabilized, polyvinyl chloride article |
US4919972A (en) * | 1986-12-23 | 1990-04-24 | M & T Chemicals Inc. | Process for surface modification of polymer articles |
US4877529A (en) * | 1988-03-10 | 1989-10-31 | Texaco Inc. | Separation of organic liquids |
-
1991
- 1991-02-27 US US07/662,206 patent/US5169688A/en not_active Expired - Fee Related
-
1992
- 1992-02-20 CA CA002061605A patent/CA2061605A1/en not_active Abandoned
- 1992-02-25 EP EP92301546A patent/EP0501735A1/de not_active Withdrawn
- 1992-02-26 JP JP4073018A patent/JPH05214130A/ja not_active Withdrawn
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB921032A (en) * | 1958-11-27 | 1963-03-13 | Tokyo Shibaura Electric Co | A method of manufacturing antistatic record discs |
FR1293186A (fr) * | 1960-04-14 | 1962-05-11 | Ici Ltd | Polymères organiques à propriétés antistatiques améliorées |
EP0134523A1 (de) * | 1983-08-04 | 1985-03-20 | General Electric Company | Absorption von Additiven aus Lösungen in Polymeroberflächen |
US4770905A (en) * | 1986-12-23 | 1988-09-13 | M&T Chemicals Inc. | Process for surface modification of polymer articles |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1994011421A1 (en) * | 1992-11-06 | 1994-05-26 | Pharmacia Biotech Ab | A method of surface modification |
US6156550A (en) * | 1992-11-06 | 2000-12-05 | Pharmacia Biotech Ab | Method of non-adhesive coating of a synthetic polymer based surface with particles |
Also Published As
Publication number | Publication date |
---|---|
JPH05214130A (ja) | 1993-08-24 |
US5169688A (en) | 1992-12-08 |
CA2061605A1 (en) | 1992-08-28 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE CH DE DK ES FR GB GR IT LI LU NL SE |
|
STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
18D | Application deemed to be withdrawn |
Effective date: 19930303 |